ArticleTetrahedron letters2011
Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones.
Article in Tetrahedron letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 112 citations in OpenAlex.
- Recent Progress in Catalytic Asymmetric Pictet-Spengler Reaction to Construct 1,1-Disubstituted Scaffolds.Synthesis · 2026Article
- A Ketone-Accepting Pictet-Spenglerase for the Asymmetric Construction of 1,1-Disubstituted Tetrahydro-ß-carboline Alkaloids.Angewandte Chemie (International ed. in English) · 2025Article
- Chiral Phosphoric Acid-Catalyzed Enantioselective Pictet-Spengler Reaction for Concise Synthesis of CFOrganic letters · 2025Article
- Catalytic Enantioselective Pictet-Spengler Reaction of α-Ketoamides Catalyzed by a Single H-Bond Donor Organocatalyst.Angewandte Chemie (International ed. in English) · 2022Article
- Site-specific role of bifunctional graphitic carbon nitride catalyst for the sustainable synthesis of 3,3-spirocyclic oxindoles in aqueous media.RSC advances · 2021Article
- Synthesis of aza-quaternary centersChemical science · 2021Article
- Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines.RSC advances · 2020Article
- The Pictet-Spengler Reaction Updates Its Habits.Molecules (Basel, Switzerland) · 2020Review
- Synthesis of six-membered spirooxindolesRSC advances · 2018Article
- Chemical probes and drug leads from advances in synthetic planning and methodology.Nature reviews. Drug discovery · 2018Review
- Phenolic Activation in Chiral Brønsted Acid-Catalyzed Intramolecular α-Amidoalkylation Reactions for the Synthesis of Fused Isoquinolines.ACS omega · 2017Article
- Isatin derivatives in reactions with phosphorus(III-V) compounds.Chemistry of heterocyclic compounds · 2015Article
- Mechanistic study of the spiroindolones: a new class of antimalarials.Molecules (Basel, Switzerland) · 2012Article
- Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.ACS combinatorial science · 2012Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-β-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.